A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes

A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetyle...

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Autores principales: Devari, Shekaraiah, Kumar, Manjeet, Deshidi, Ramesh, Rizvi, Masood, Shah, Bhahwal Ali
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273296/
https://www.ncbi.nlm.nih.gov/pubmed/25550726
http://dx.doi.org/10.3762/bjoc.10.277
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author Devari, Shekaraiah
Kumar, Manjeet
Deshidi, Ramesh
Rizvi, Masood
Shah, Bhahwal Ali
author_facet Devari, Shekaraiah
Kumar, Manjeet
Deshidi, Ramesh
Rizvi, Masood
Shah, Bhahwal Ali
author_sort Devari, Shekaraiah
collection PubMed
description A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetylenes , i.e., arylacetylenes and most importantly aliphatic alkynes.
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spelling pubmed-42732962014-12-30 A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes Devari, Shekaraiah Kumar, Manjeet Deshidi, Ramesh Rizvi, Masood Shah, Bhahwal Ali Beilstein J Org Chem Letter A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetylenes , i.e., arylacetylenes and most importantly aliphatic alkynes. Beilstein-Institut 2014-11-12 /pmc/articles/PMC4273296/ /pubmed/25550726 http://dx.doi.org/10.3762/bjoc.10.277 Text en Copyright © 2014, Devari et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Devari, Shekaraiah
Kumar, Manjeet
Deshidi, Ramesh
Rizvi, Masood
Shah, Bhahwal Ali
A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes
title A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes
title_full A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes
title_fullStr A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes
title_full_unstemmed A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes
title_short A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes
title_sort general metal-free approach for the stereoselective synthesis of c-glycals from unactivated alkynes
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273296/
https://www.ncbi.nlm.nih.gov/pubmed/25550726
http://dx.doi.org/10.3762/bjoc.10.277
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